35 Year Old Virgin
by Althe
Summary: Sasuke has been single for 35 years and Shinobi across the land are trying to help him out in the lady's department. Unfortunately love is hard to find when she's married to your best friend. Will the last Uchiha ever find love?
1. Drink up

**35-Year-Old-Virgin**

**Chapter One: Drink Up**

_The beginning may be a little rough due to new character introductions, but the ends a classic. Read on! =)_

**-----**

Sasuke fiddled with his kunai, swinging it absentmindedly with his finger as he stared across the field at a group of women settling down for a picnic. Their long hair blew with the gentle wind. He could smell rice vinegar and barbequed fish.

A rock hit him sharply on the back of his head.

"Sasuke-sensei! How can we learn anything when you're always spacing out?" Kana scolded, picking up another rock and throwing it at him. Sasuke caught it with ease, tossing it to the ground.

Kana had her arms folded, Rena and Sachiko standing beside her. He was in charge of team 7, who were all fresh from their chunin examination.

"Sorry Kana- and it's Uchiha to you," Sasuke says, getting up from his spot on the grass. He rummaged in his pocket as he continued to speak. "Here's today's lesson…" he reveals two silver bells dangling from red strings. "Each of you must take a silver bell from me."

"Uchiha-sensei," Rena noted, "there are only two bells."

"I guess one of you's out of luck then." Sasuke jumped a foot away from the girls and held the two bells high up in the air. "Let the game begin!"

The three looked at each other, then charged at him. Even without his sharingan, their moves were predictable. He dodged them with ease, even managing to ruffle Kana's hair as he passed her and jumped up into a tree.

"Losing girl gets no lunch on me," Sasuke called out. This got their attention.

Not far, the real Sasuke laid back from behind a low hill, continuing his picnic watch. Kage bushin no jutsu had its many uses.

Their laughter and voices drifted with the gentle wind. He could see Sakura amongst them, eating a sandwich next to Hinata. How many years had she been married to Naruto now? How weird. She had spent so long loving him, he always thought that would never change.

Her wedding ring glistened in the sunlight and he couldn't help but feel a pang of envy. All those women, at one point -minus Hinata- had been in love with him. Now, he was no better than his brother. Crazed genius workaholic with antisocial tendencies and ostracized by most of the older generation for atrocities of the past. He was lucky that Naruto was the hokage or else he may as well been given death row.

Sakura noticed him and gave him a friendly wave. He returned the wave, feeling like a child given praise from a favourite teacher. He sometimes wished he hadn't taken his charmed looks for granted. Why didn't he try going out on a date? Talking to a girl? At the very least scoring with one. His first and only kiss was still from Naruto for christ's sake.

Silver bells rang in the distance. Sasuke looked up to find his clone flying through the air with three girls tailing him. This could be a while. Kana screamed in frustration, throwing kunais in his clone's general direction. All missed and hit a tree trunk. Sasuke felt his lips curl slightly into a shadow of a smile. For a moment, he saw Naruto in her enthusiasm. They were so uncoordinated back then, fighting more with themselves than trying to get the silver bells from Kakashi's swift hands.

After an hour longer with no luck, Sasuke decided to wrap the activity up. The women were already finished their picnic anyways.

"Okay girls, time's up," Sasuke called, catching the bells that his clone threw him before disappearing.

"What the-? No fair Sasuke-sensei! You were cheating!" Kana screamed, pointing a threatening finger at him.

"If you couldn't get the bells from my clone then you definitely wouldn't have been able to get it from me," Sasuke said, ruffling her hair once more. She shakes her head to get his hand away. "And it's Uchiha Kana. Let's go for sushi."

"I'll go home for lunch sensei," Rena said meekly, her cheeks glowing red. Sasuke gave himself a mental slap on the head.

"No, don't do that Rena. Lunch's on me- for cheating a little." Rena's face only glowed more, but she nodded.

"Damn right Sasuke-sensei! That'll teach you to be a cheater," Kana said, punching him playfully on the arm.

"Quiet Kana. You're too noisy- and it's Uchiha to you."

-----

Sasuke exited the sushi restaurant, waving goodbye to team 7 as they went the opposite direction. He strolled down New Konoha, admiring the scenery around him. There were still a few more hours of daylight left and he was at a lost with how to spend the rest of his day. There was always training by the waterfalls, studying ancient technique scrolls, finishing his mission paperwork-

"Sasuke!" he turned to find Shikamaru and Kiba heading towards him.

"Yo," Sasuke said, giving them a curt wave.

"We're heading out for some drinks with the other guys. You wanna join us?" Kiba asked.

"Oh, sure," Sasuke said slowly. He wasn't used to being spontaneously invited to social events let alone going to one. He was usually so caught up in his work, no one bothered him.

The three nodded and walk down the road together. He could feel his awkwardness seeping out of him with each step. Shikamaru and Kiba chatted up a storm as Sasuke listened with interest.

"So I hear Gaara's in town for a bit," Kiba said.

"Yeah, he's joining us for beer," Shikamaru mumbled, lighting the cigarette between his lips. He took a long drag and blew out a thin line of smoke up into the air. "Lee, Neji, and Choji are coming as well."

"What about Naruto?" Sasuke asked. The two glanced behind at him.

"Of course," Shikamaru replied, "that social butterfly never misses an event."

Yeah, of course. It was funny how Sasuke and Naruto seemed to had switched positions from childhood. The nine tailed fox boy had finally broken the status quo and rose to the top of everyone's admiration and respect. He never thought less of Naruto, not since their first mission into the mist village.

"You'd think he'd be a lot more productive now that he's hokage," Kiba remarked, "all the bastard does is party with old farts like us." He said this with a grin.

"Kiba, don't depress me with age talk. I'd like to think 35 is a young ripe age," Shikamaru sighed, taking another long drag on his cigarette.

They arrived at the bar, finding Choji and Neji sitting down at one of the large private booths. Sasuke seated himself next to Shikamaru as Kiba slid him a cold beer from across the table. He watched briefly as Shikamaru cracked his open with the edge of the table before following suit. It's been a while since he had a drink.

"So where's everyone else?" Kiba asked, taking a swig at his beer.

"Coming with Naruto I suppose. Gaara just arrived today. It's some hokage business," Choji said, too preoccupied with the menu to elaborate.

Sasuke sipped his beer silently, trying not to wrinkle his nose at the unfamiliar aftertaste.

The other four had matured exponentially over the years. Choji lost a significant amount of fat and bulked up into nothing but muscle; Shikamura's voice became low and husky (probably from all the cigarettes he smoked) and had a good sized beard that framed his face; Kiba…well, not much changed with Kiba except he stopped face painting (but it was amazing how much better he looked without it); and Neji finally got rid of his ridiculously long hair and opted for a shorter, more stylish one.

Sasuke on the other hand looked more or less the same. He had more wrinkles from age and stress, but other than that, he and his thirteen-year-old self were identical. Some would say being ageless was a gift, but he considered it depressing.

"Hey guys!" That familiar voice. Sasuke didn't need to turn around to know it was Naruto. "Did you have to wait lo- Sasuke! Good to see you!" He took the seat next to him, giving Sasuke a rough shoulder hug. "My man Sasuke!"'

Gaara and Lee were with him and they took the seats across from Sasuke.

"Good to see you too Naruto," Sasuke said, giving his best friend a warm smile. They had talked just yesterday, but that meeting was strictly business.

Since Naruto's crowning of hokage, Sasuke began seeing less and less of him. It wasn't until Sasuke left Anbu's specialist squad that they started making more face time with one another.

Just like the others, Naruto had also matured greatly. His hair was more kept and his size bulked. Sasuke could tell Naruto's blue eyes and blond hair were finally catching the eyes of many women, but the silver wedding band around his left ring finger kept them at bay.

Gaara held his beer out towards Sasuke, saying, "Sasuke, long time no see."

"Same to you," Sasuke said clinking his beer with Gaara's before taking a drink.

"Here's a toast to good friends!" Naruto shouted, raising his beer in his outstretched hand. There's a symphony of clinking bottles, then everyone downed their beer.

"How's the missus hokage-sama?" Kiba asked, emphasizing the suffix with much enjoyment.

"Sakura-chan's great. We're planning to get a little Naruto soon, but she still wants to focus on her work a bit more." Naruto looked out with a dreamy glint in his eyes, smiling with the beer bottle in his mouth.

"One Naruto is enough. I don't think we need another one," Sasuke joked.

"Well we definitely don't need another Sasuke either," Naruto shot back.

"I think your wrong Naruto," Neji said, popping open another beer, "Sasuke's the most productive ninja on the force. He gets more done that Shikamaru- when the guy actually puts his mind to doing work." Shikamaru lazily fingered Neji, putting more conviction into drinking his beer than in the gesture.

"Are you seeing anyone Sasuke-san?" Lee asked. It was so formally asked, Sasuke felt obliged to answer.

"Ah…no…not really."

"Not really? What does that mean?" Naruto questioned, staring Sasuke down hard with his squinted eyes. Sasuke felt like squirming.

"So is there someone you like?" Kiba asked. Sasuke shook his head, hastily drinking his beer.

"Now that I think about it, I don't think I've ever seen you with a woman before," Shikamaru noted, lighting up another cigarette.

"That reminds me, the last time I saw you with someone was with Temari. How are you both?" Rock asked Shikamaru.

Choji turned his attention away from the menu, saying, "Shikamaru and Temari broke up ages ago," before waving for a waitress and turning back to the menu.

"Yeah, things weren't so hot with Temari and I with the whole long distance issue and all," Shikamaru replied, tilting his head at Gaara. "Sorry man. I know it disappointed you."

Gaara shook his head. "Don't mention it. It was ages ago. She's fine now," he added when he saw Shikamaru's concerned look.

"So why haven't you been on the dating scene?" Kiba turned the hot spot back on Sasuke. "You used to be so hot with the ladies."

Sasuke focused his attention on his beer, mumbling, "They didn't interest me."

"So you're gay?" Everyone stopped their drinking to look closely at Sasuke. He scowled at Kiba.

"Don't disgust me, of course not. I've just never familiarized myself with that area."

"You're making it sound like some kind of study Sasuke," Naruto chuckled. Sasuke shot him a glare as well.

"I don't see what's the big hype about. Dating is only distracting." Sasuke could feel himself getting defensive, but he couldn't stop.

"That's virgin talk Sasuke-"

"I'm not a virgin," Sasuke snapped, downing the rest of his beer. He avoided eye contact with the others, keeping his attention on the table.

Naruto smirked, tossing his friend another beer.

"Time for a drinking game guys," he calls, "Let's play 'I never', except we play 'I have'. Drink if you've done it."

"Ass." Naruto ignores Sasuke, taking a long drink along with everyone else as Sasuke stares in dismay. They all look at him confused at whether or not to be smug about their new discovery. Sasuke looked curiously at Choji and Gaara.

"Ino," he said curtly.

Gaara said nothing, only giving him a quick wink that sends a cold shiver down his spine.

"Wow, never Sasuke? That's pretty amazing," Kiba whistled.

"Yeah, well, I had better things to do," Sasuke mumbled, fiddling with his beer.

"Don't worry Sasuke-san. We can help you," Rock Lee assured, placing his hand on Sasuke's and giving it a tight squeeze. Sasuke almost thought Lee was offering him a business proposal. The guy had to stop being so damn formal with such indecent discussions.

"Yeah, Rock's right. Let's help Sasuke get laid," Naruto said the last part loud enough that the whole restaurant turned their attention to the table. Sasuke swung his bottle at Naruto. His face felt so hot, he could barely see through the steam.

"Here, here!" The table raised their glasses once more, taking a long swig in Sasuke's honour.

Sasuke felt a headache coming. And it wasn't from the beer.

**-----**

_Please R&R! =) Suggestions and constructive criticism welcomed  
_


	2. Date 1: Temari

**35-Year-Old-Virgin**

**Chapter Two: Date #1 Temari**

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**

White sunlight peaked through the drapes, blinding Sasuke as he tried to open his eyes through the glare. He glanced at the bed stand clock, which read 6am. Immediately, he pulled the covers over his head; this was way too early for a Sunday morning.

Just as he's about to doze off, there is a knock on his window. He looked up to see Naruto grinning at him from behind the dusty frame.

"Good morning Sasuke," Naruto chirped as his friend unlocked the window.

"Yeah…morning Naruto. Do you know what time it is?" Sasuke rubbed his eyes thoroughly, noting Naurto rummaging through his now disheveled closet.

Naruto tossed him his casual wear, replying, "Yeah, time for us to head downtown for breakfast."

Sasuke gave him a quizzical look, slipping on his t-shirt and jeans. The sixth hokage continued to smile mischievously, only shrugging in reply.

He opened the door for Sasuke and the two head out towards the market area. Citizens were already busy opening up their businesses, the streets bustling with activity.

"I want to take you to my favourite restaurant," Naruto said, waving to several passerbyers who stopped to bow.

"Why are we getting so fancy in the morning? Why not just go to one of your regular ramen stands?" Sasuke asked absentmindedly, nodding his head to a few acquaintances.

"Those places don't provide a lot of privacy. Besides, we're meeting up with Shikamaru, Lee…"

"Shikamaru and Lee?" Sasuke repeated.

"Oh, and Gaara," Naruto added.

"Gaara? What is this about?"

"About you still being a virgin." Sasuke stopped walking, causing the man behind him to bump into his back. Naruto turned and quirked his eyebrow at his friend's stunned face. "What's wrong Sasuke?"

"Naruto," Sasuke breathed, feeling the pulse of his temples with his fingertips, "Why are we discussing such personal matters- let alone with Shikamaru, Lee, and the Sand Hokage?"

"Well," Naruto shrugged, "From what happened last night, we thought you could use our help."

Sasuke leaned close to Naruto, hissing, "Last night? We?"

"We all kind of found out you've never been with a woman before- and by we I mean all the guys like Choji, Neji, Kiba, Shikamura…hm…Shino, Kankuro, Konohamaru, and Sai probably know by now-"

"Jesus Christ Naruto-"

"But don't worry," Naruto assured, "it's only between the guys. We stick together, no?"

Sasuke could only cover his eyes, keeping his gaze firmly planted on the ground as they continued their walk. He didn't want to look at anyone- ever again.

Shikamaru, Lee, and Gaara, look up when Naruto and Sasuke enter the Chinese restaurant, taking their seats at the private booth.

"Greeting Naruto-san, Sasuke-san. I apologize for the lack of numbers, but some of us couldn't get up this early on a Sunday morning," Rock said. A waitress came and offered them all tea.

"That's quite all right Lee," Sasuke mumbled.

"I'm surprised you're even here Shikamaru," Naruto said.

"What, and miss this? I haven't seen this much action- well lack of action." This did not please Sasuke.

Gaara waved his hand for service, saying, "Naruto told me this restaurant has excellent Chinese food, so I came."

"Four beers," Sasuke said the moment the waitress came to their table.

"Whoa Sasuke. This early in the morning?"

Sasuke glared at Naruto, saying, "If we're going to continue on with such a vulgar conversation, then I'll need something to keep me mind-numbingly sane. And they're all for me by the way."

Everyone made their orders before continuing on with the discussion.

"Okay, who's single and in our age category?" Naruto asked.

"Hinata's available," Shikamaru said, "but I think she's still in love with you hokage-sama."

"No way, it's been ages," Naruto shook his head, "What do you think Sasuke?"

"Kill me," he replied while he downed his beer. It had been so long since he's drank so frequently, but the addictive affects were already kicking in.

"I believe Temari is single, right Gaara-san?" Rock suggested.

"Er, I prefer not to put her as an option."

"Shikamaru, if you're not going to court my sister, don't keep her locked in a cage," Gaara said, glancing his way. Shikamaru shrugged, fumbling in his pockets for a cigarette.

"Tenten?"

"Naruto-san, I think we would need to discuss that with Neji-kun. They dated for a while and I'm not sure if everything has settled between them."

"Jesus, why can't everyone just have clean break ups?" Naruto yelled, slamming his fist on the table. "I should create a festival gathering single women with no strings attached."

"Yes, and that's an excellent way to abuse your hokage powers," Sasuke said, popping open his second beer.

"Too bad you couldn't have gotten Sakura while you still had the chance and I would have gone with Hinata, eh Sasuke?" Naruto joked. Sasuke would have laughed with him, but it was too close to the truth for comfort.

"If you don't mind a long distance relationship, I'm sure my sister wouldn't mind giving this a shot," Gaara said, ignoring the glare Shikamaru shot him. "She's coming to visit this evening to escort me back tomorrow morning."

"Awesome, isn't this great Sasuke? Your first date."

"Shut up Naruto."

-----

Sasuke was back in front of the Chinese restaurant, fumbling with his uneven tie as he watched the red sun slowly disappear behind the tiled rooftops.

The others had somehow talked him into getting dressed for the occasion, but the form fitting dress shirt and pants only suffocated him. He loosened his tie a couple of notches and breathed a sigh of relief.

"Already calling it a day?"

Sasuke turned and found Temari standing before him. She was still in her training gear and a little dusty from the long trip.

This wasn't fair. She was allowed to look sloppy and he was required to look like some pompous tight ass? Dating was already beginning to seem like complete bullshit.

"Ah, long time no see Temari," he said, adjusting his tie back to its proper place. He opened the door for her and slipped into the restaurant right after. _Gentleman manners, gentleman manners, _he repeated to himself, recollecting all that Rock Lee taught him the past few hours.

They took their seats at a small table and ordered their dinner before resuming the conversation.

"So what's new with you Sasuke?" Temari inquired, resting her chin lightly on her folded hands.

"Still training young ninjas. My team recently passed the chunin exam. How about you?"

"Congratulations. I'm still working closely behind the hokage. There hasn't been a lot going on lately, so my job's only been traveling alongside Gaara. Kankuro's the one handling more important missions."

"Really now? Why aren't you out completing missions? You more than capable," Sasuke said, sipping his tea.

Temari shrugged, "Don't know. I haven't done anything for the past four years, I guess I'm getting used to it."

The server presented them with warm rice wine and a few appetizers. Sasuke immediately poured Temari a small glass and she accepted it graciously.

"Did something happen back then?"

"Hm…I wonder…," Temari sipped her rice wine, staring over Sasuke's shoulder with unfocused eyes, "I guess I was more focused on personal matters than my role as a ninja."

"It sounds like you've been through a lot of hardship."

Temari turned her focus at Sasuke and stared at him cautiously.

"I knew something was wrong. Why are you talking so much? This is really out of character."

"Lee told me women enjoy a lengthy intimate conversation and so I'm following his advice."

Temari suppressed a laugh, but Sasuke just waved his hand, giving her the go to begin her guffaws.

"I know. It sounded ridiculous to me as well."

"No Sasuke, you've got it all wrong," Temari chuckled, "I think it's really sweet"

Sasuke raised his eyebrow. "You do?"

"Well, it's funny, but it's nice that you're putting in the effort. It's been a while since I've seen such courtesy in a man."

"What, did Shikamaru only offer you cigarettes?" Temari frowned at his comment, causing Sasuke to hastily say, "I'm sorry. I crossed the line."

"No," she shook her head, "it's alright. I'm just remembering my time with Shikamaru."

"Are they bad memories?" He never really cared about what went on with Shikamaru and Temari, but their relationship did cause quite a stir in both the leaf and sand village.

It had potential to be a political fortune, solidifying good relations between both villages seeing as Temari was the sister of the current hokage and Shikamaru was the squad leader for Anbu. Obviously things never worked out between the two, which was a great let down for both sides. Again, it didn't affect Sasuke, but he couldn't help but feel pity for Temari.

"Actually no," she finally said, "just sad thoughts and regrets."

Sasuke urged her on with another raised eyebrow.

"I guess it hurt because I thought it would last- and there was all that pressure from the politics. I thought if I cut back on my work we could see more of each other, but Shikamaru kept firm with his career…and the gap between us just grew. Our last year together was really rocky and he finally ended the relationship. I planned to get my career going again, but it just never happened. I was probably hoping he would change his mind."

Sasuke nodded sympathetically as he refilled her glass, all the while trying to remember any phrases Lee taught him that would comfort her.

"You look very lovely today," he finally said.

"Excuse me?"

"Ah, I mean, I think you're wasting your time waiting for someone who obviously doesn't care-" _Sasuke-san, that's too harsh! _He could hear Lee scolding him in his mind. "-I'm sorry, what I meant to say was-"

Temari pressed her fingers to his lips, silencing him. Luckily, she wasn't frowning.

"It's okay Sasuke. You don't have to say anything to try and comfort me. I've come to terms with my situation and I agree with what you say. I was just wasting my time," she gave him a soft smile, pulling her hand back to her side.

Sasuke rubbed his lips together, flustered by the sensation of warm fingers intimately touching his face.

"You're a strong ninja with unique techniques Temari. It would be a shame to see you away from the force. You have so much ahead of you as a shinobi of the sand village."

"Ah, yes. The life of a ninja," Temari sighed.

"What do you mean?"

"We work so hard to become excellent shinobis, dedicating our life to our village, we often live the lonliest life because we can never focus on ourselves."

"That's not true," Sasuke corrected, "we're always focusing on ourselves, perfecting our techniques and improving our physique."

Temari chuckled, "No Sasuke. Not like that. We never have the time to focus on our social well being. Like our family and friends. Our comforts and wants."

"I don't quite understand. I've never thought of such matters before."

She picked a dumpling and placed it on Sasuke's plate. He soaked it in soy sauce and paused for a moment, suddenly remembering something Naruto said to him. He then raised the dumpling to her lips. Temari looked at Sasuke, but tilted her head forward and took the dumpling from his chopsticks.

"Tasty," she said, licking her lips.

God, why did he have to feed her like she was three?

"Very smooth for someone who's never been on a date before," Temari noted, holding a dumpling up for him to eat.

He stared hard at the dumpling, taking it with his chopsticks.

"Who told you I've never gone out on a date?"

"Gaara mentioned it earlier."

"….what else did Gaara mention?"

"That you're a 35-year-old-virgin."

Sasuke choked on his dumpling at mid-swallow.

"What? What's wrong?" she asked as he sank his face into his hands.

"He wasn't supposed to tell you that," he said, glaring at her through the slits between his fingers. Temari laughed, refilling his glass with more rice wine.

"Don't worry so much. Gaara didn't say it on purpose…he just let it slip-"

"Just let it slip?"

Temari gently took his hands into hers, stroking them gently. He kept his eyes to the ground, his cheeks burned and his eyebrows furrowed.

"He's my brother, Sasuke. I can pry anything out of him. Besides, he asked me to go out for dinner with you, there had to have a reason."

"What about, 'it's been a while since you've seen Sasuke' or 'you haven't gone out in a while' or 'it's just fucking important business'?"

"I don't judge Sasuke. So you've never slept with anyone before-"

"I prefer you don't mention it again."

"Right."

They finished their meal with a lighter air, Sasuke attentively steering the conversation away from any intimate topics. Temari offered to pay for half the meal, but Rock Lee's voice boomed in his head, stating, '_you should always pay for the meal. It is law Sasuke-san!' _Again, total bullshit in Sasuke's eyes, but he paid anyways. He opened the door for her and they exited the restaurant.

Shadows engulfed the sky, casting elongated dark figures down the street. '_Sasuke, midnight strolls are the perfect opportunity to get close. Hold her hand, take her home, do you understand me?' Yes, Naruto. Yes, I do, _Sasuke sighed. They were walking down the street, side by side. He glanced down at her hand swinging back and forth, took a deep breath, and clasped it in his. Temari gave him a sideways glance and he responded with a raised eyebrow.

"Is there something wrong?" he asked.

"Well, you're holding my hand all wrong."

He looked down again and saw that he was squeezing her hand with white knuckles like he was holding onto a stress relief ball. He immediately released his grip, mumbling a soft apology.

"Here…" Temari shook her head, grabbing his hand and intertwining her fingers with his. "This is how you hold a lady's hand."

"This is strange," Sasuke said, "if we were attacked, I would lose two seconds trying to get out of this grip."

"Wow, Sasuke. You were so close to being such a smooth talker."

They arrived at the front entrance. Temari paused before unlocking the door, asking, "Do you want to come in for some tea?"

"No, thank you-"

The door opened and Gaara appeared before them. He stared at his sister and then looked Sasuke up and down, saying, "Ah. So you're back from your date."

"Hey Gaara," Temari said, waving at her brother.

Sasuke released their handhold and mumbled, "I'm going to get going now…"

"Oh, okay. Thank you for dinner Sasuke." Temari leaned forward and gave him a quick peck on the cheek. "I really enjoyed myself tonight."

"Me too," he replied. Sasuke paused a moment, then decided to give her a quick pat on the back.

She disappeared into the room, which left him and Gaara standing alone in the hallway. Sasuke nodded his head at him, saying, "Good night Gaara."

"Good night Sasuke," Gaara whispered, leaning forward and planting a soft kiss on the unsuspecting man's cheek.

He quickly returned to his guest room before Sasuke could react.

Gaara was really starting to freak him out.

**-----  
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_Thank you for reviewing Lupinwolf3992! More updates to come! I apologize for constantly reuploading these last two chapters, but the grammar mistakes and awkward phrasing were really killing me._

_If you have any requests with who you want Sasuke to date next, please let me know =)_

_**R&R!!!!**  
_

**Next Chapter: Covering the Bases & Date #2  
**


	3. Covering Bases and Date 2

**35-Year-Old-Virgin**

**Chapter Three: Covering the Bases for Date #2**

"Forget it, I'm not seeing Tenten." It had only been a week since his first date and Naruto was already trying to set him up with someone else.

"Come on Sasuke. Temari can't visit Konoha often and you need to broaden your options. We don't have time to waste."

"Don't have time to waste? I never knew there was a dating time limit," he muttered.

Naruto flipped his okonomiyaki, patting the uncooked side down into the fryer. He poured more oil on the hot metal before saying, "No, no. There just isn't enough females to go around, you know?"

"I don't know," Sasuke said flatly, flipping his pancake before it started to turn dark brown.

"Kishimoto didn't create a lot of female ninjas for the series. I mean, quite literally, we only have four girls our age to pair you up with (minus Sakura cause I married her) [A/N: Not including any extra female characters from the anime]."

"No kidding."

"Exactly. So we need to act now," Naruto nodded approvingly at his plan.

"Does Temari know about this?"

"Yeah. But Tenten doesn't, and I think you better keep it that way."

"Hm? Why?"

"She's a bit possessive from what Neji tells me."

"Is this bit of information supposed to make me want her more?"

"All girls are possessive to some degree Sasuke. You're just going to have to get used to it," Naruto chuckled. He took a large bite of his okonomiyaki, quickly spitting it back out from the burning heat. Sasuke frowned at the sight of the half eaten pancake, already losing appetite for his own.

"What, is Sakura possessive too?" Sasuke inquired. He tried to make his voice casual, keeping his attention focused on eating his meal.

Naruto paused from his okonomiyaki making, thinking hard before answering, "No actually. She's never gotten jealous, but she is really strict. I mean, I can't leave my clothes on the bed without her complaining about it. I get a earful from her everyday about my carelessness."

"How does that make marriage appealing?"

Naruto smiled. "She yells at me, but it's all fun. Behind the bickering is love, you know? She wouldn't do it unless she cared."

Sasuke said nothing more and finished his okonomiyaki and downed his beer. After a while, he looked up at Naruto. Seeing his best friend's gleaming face gave him mixed feelings. Half of him wanted to punch his face and the other half…well…. He was starting to relate to what Naruto meant about yelling, but still caring.

"Fine," He finally scowled, "hook me up with Tenten."

-----

"Sasuke-Sensei!"

Sasuke looked up from his book, startled at the sudden ring in his ears. Kana was standing before him, her hands on her hips as if she was about to scold a delinquent.

"You're ignoring us again! Why do we even put up with you if you don't even teach us anything?!"

He closed his book slowly, sighing, "You're already done walking the dogs?"

Kana threw her arms up in the air in frustration. "I can't believe we still have to do these stupid missions! We're chunin already! Why can't we go on the higher level ones? This is so retarded Sasuke-sensei!"

"Watch your language Kana- and it's Uchiha-sensei. Missions have been slow lately. I promise when an overnight mission comes up, I'll be the first to get it and let you guys know, okay?" This reassurance did not satisfy Kana. She frowned at her slack teacher as she crossed her arms.

"You've been distant Uchiha-sensei. Is something wrong?"

Sasuke turned his attention to Sachiko, who was a good head shorter than Kana (she and Rena were also five years younger. Kana started school a lot later than the others due to medical complications as a child).

He shook his head, smiling at her.

"No Sachiko. Everything's fine. I've just been busy, that's all."

"Busy? It's three o'clock and all you've done is read that book. How can you be busy?" Sasuke jumped up, causing the other three girls to jump back.

"Three already? Crap, I'm late." He ran past team 7, hastily waving goodbye to the three. "I'll see you guys tomorrow."

"Sasuke-sensei! Where are you going?!"

"Sorry Kana, I have a date! And it's Uchiha-sensei!"

-----

Sasuke knocked on the front door and was immediately greeted by Tenten. He had to do a double take of the girl standing before him.

She had her chestnut hair down, which curled to her chest. Just the hair made a big difference to Tenten's once childish features, but her body had also toned to an hourglass proportion. She wore a hint of makeup that emphasized her pouted lips and full cheeks. Blushing, Sasuke looked away, muttering a hello.

"Long time no see Sasuke," Tenten nodded, "can you wait a minute? I just need to grab my purse."

Sasuke felt a rock sharply hit his head as Tenten disappeared behind the door. He shot a fiery glance behind him only to find a bouquet of flowers a few feet away. Walking over, he picked it up, carefully opening the note that was attached.

_Don't forget your manners._

It was in Naruto's handwriting. Go figure.

Crumbling the note, Sasuke went back to the door just as Tenten reappeared. He held up the bouquet, surprised at the warm expression that immediately blossomed from Tenten.

"How thoughtful of you Sasuke! I never knew you could be so sweet!" She took the bouquet and took a whiff, smiling at the sweet scent of lilies.

After putting the flowers in a vase, the two walked down the street towards the park. Tenten made no attempt to hold his hand and he made no attempt to hold hers. He felt more comfortable that way, but Rock's voice wouldn't stop booming in his mind: _Make her feel special Sasuke-san! She will never open up to you any other way!_

"So…how….what have you been up to?" he asked.

"Oh…nothing much."

Wow. What was he supposed to say now? Should he even bother to keep up with a conversation she was making no effort at?

Hm…nah.

They got to the park and went down towards the lake where a vendor was renting out swan boats. Seeing Tenten's eyes sparkle gave Sasuke the fleeting impression of Naruto at the sight of a hearty bowl of ramen.

He took her hand and led her towards the dock. He paid for a swan boat and the two got on and started paddling.

"This is really fun!" she chirped, looking out at the lake water.

"Yeah, sure," he said, staring out at the water as well, but with a less enthused expression.

They spent an hour out in the water, keeping conversation to a minimum. Tenten hummed a tune every now and then, but it did little to subside Sasuke's wish to have his hour back. As they were pulling towards the docks, Tenten stopped her paddling, causing the boat to rotate slowly around 360.

"Is everything okay?" he asked, stopping his paddling.

"You want to play a game?" she gave him a mischievous smile, but he went along with it anyways.

Tenten stood up on the boat, putting one foot on the ledge. She motioned for Sasuke to do the same. The swan rocked dangerously as the two tried to balance on opposite sides of each other.

"Now…" Tenten put both feet on the ledge and Sasuke did the same. They both stared at each other, Sasuke giving her a quizzical look. "Let's see who can keep balance for the longest. Anything goes. You ready?"

"Sure." Sasuke had barely time to answer and Tenten had already chucked a kunai at him. He bent back, suspending his body in a boomerang shape. The kunai grazed the hairs on his chin, sending a chill down his spine.

"Tenten, what the hell?"

"Come on Uchiha Sasuke. Give me your best shot," Tenten shouted, sending him another kunai. Sasuke blocked it with a kunai of his own.

"Tenten, you're insane!" Sasuke plunged his weight down onto the boat, sending Tenten's side high up into the air. She still managed to keep her balance, all the while sending a low kick towards him.

He grabbed her foot and swung her into the lake. His sleeve caught her bracelet just as he released her and he soon found himself gasping for breath in the deep blue. Tenten popped up right beside him. She chuckled at his stern expression, cutting the developing tension by splashing him with water.

"Guess you win," she said.

Sasuke swam towards the boat and hoisted himself up. He pulled Tenten out, but she slipped on the ledge. The two tumbled to the boat floor where Tenten's body pressed against Sasuke's. Their wet clothes clung to each other. A moment went by where they locked eyes, both barely breathing.

"Am I supposed to kiss you now?" Sasuke finally asked.

"Why are you even asking?"

-----

"Noodles up!" the cook passed the five bowls along the noodle stand. Sasuke took his bowl and passed the others to Shikamaru, Sai, Rock, and Naruto.

"So how did it go with Tenten?" Shikamaru asked as he passed along the bottles of beer.

Sasuke took a sip before saying, "It was alright."

"What do you think? Is she the one?" Naruto asked.

"The date wasn't that eventful in the beginning. I really don't know. I think I enjoyed my date with Temari more."

"Really?" Shikamaru seemed a bit disappointed. Sasuke gave him a quizzical look.

"What, were you planning something with her?"

Shikamaru shook his head.

"So how far have you gone. First, second base?" Naruto asked, nudging Sasuke with his elbow.

"What are you talking about?"

"You know…."

"No, I don't know."

"Haven't you heard of the bases before?" Naruto seemed baffled.

"If I did, then I wouldn't be asking Naruto."

"I believe the bases represent the physical milestones you have passed with your partner. First would mean you both have kissed, second involves more intimate physical contact, third is oral, and home run is when both have intercourse," Rock said, making unnecessary hand gestures that went along with his thorough explanation.

"Lee, must you always talk like that?" Sasuke sighed, feeling his cheeks burn slightly.

"I apologize if it offends you, but I always talk like this Sasuke-san."

"Well, stop. It really doesn't fit the atmosphere."

"I don't see why this whole dating business has to have such complicated technicalities," Sai said, "I mean, if you like the girl, great. If not, then why bother?"

"You might grow to like the person Sai," Naruto said.

"That seems silly. Why put in the effort to like someone if you don't like them in the first place?"

"Maybe this dating advice should go to Sai, not me," Sasuke sighed.

"No thank you. I'm happy with my life as it is."

"Funny you say that because I thought I was happy with mine too, but obviously the others disagree," Sasuke muttered, giving Naruto another one of his glares.

"Sai's weird Sasuke. Guys like you were meant to settle down," Naruto said

"Oh really?" Sasuke still remained unconvinced. He ate his noodles silently while Naruto slurped his second bowl in obvious contentment.

"So Bachelor-san. Have you made it to first base yet?" Sai asked as he rested his cheek on his propped arm.

Sasuke didn't answer. This brought a whistle out from Shikamaru.

"How about second base?" Naruto prodded.

"No."

"Who was it with?" Shikamaru asked as he lit up a cigarette.

"None of your business."

The men finished their meals and called it a night. Sasuke left feeling more irritated and confused than in the morning. How did he stumble into this catastrophe? All these dates and late-night hangouts with the guys only hindered his work- not to mention piss his team off. And yet he was loving every minute of it. Was he turning into a masochist?

He paused a few steps from his door, surprised to find a visitor waiting for him. It was Sakura.

**-----**

_**Another chapter completed! Thank you for being patient with this new update. If you have any suggestions on who Sasuke should date next or any other kind of requests, send them my way (cause I may be losing ideas fast)**_


	4. Dating Hinata

**35-Year-Old-Virgin**

**Chapter Four: Dating Hinata**

The moon's pearl glow reflected on her pale skin and pink hair. Sakura's luminescent face reminded him of a mermaid underwater. He approached her with a delicate caution, afraid to break the calm.

Sakura turned her attention to Sasuke and grinned. Her eyes had a small twinkle that brought a shadow of a smile out of him.

"Can I help you with something?" he asked.

Sakura shook her head and stepped away from the door to allow Sasuke to enter. He turned the lock and opened the door for her.

He locked up behind him and kicked off his boots in one lethargic motion. Right beside him, Sakura took her time removing her sandals, placing them neatly perpendicular to the entranceway.

After making a teapot of matcha, the two sat down at the kitchen table. He took a long drink and refilled his cup, but the dry itch at the back of his throat would not dull.

"How are things going for you Sasuke? Naruto said you were trying the dating scene now," she said, sipping her tea as her eyes drifted off to a distance.

Sasuke thought a moment before replying, "Yes…well, your husband insists on being the kind Samaritan… and help me settle down."

"Oh? You want a family?" Sasuke saw her eyes flicker, but wasn't sure if it was a good reaction or not.

"I'm not jumping for the idea. I can't remember what a family is so I don't have a preference."

She gave a small chuckle as she set her tea down from her wet lips. Sasuke absentmindedly licked his own, feeling the cracked skin scratch at his tongue.

"You always worried me with your indifference to everything Sasuke," she said, smiling softly.

He looked away and asked hurriedly, "How are you and Naruto?"

"Oh…we're okay. Naruto's really kind to me."

"I heard you both were going to try for a kid soon."

Sakura didn't respond. She circled the lip of her cup with her finger, following the circular motion with unnecessary concentration.

Sasuke bent his head and tilted it so that he could see her face better. He asked, "Sakura? Is something the matter?"

She shook her head slowly and said, "No. Nothing's wrong… but I think I should go. It's getting late."

Sakura rose from her seat, bowed and thanked him for the tea. He thought it was odd to come all this way for such a short visit, but he didn't protest for her to stay longer. Before exiting, Sakura paused and gave Sasuke a long hard look.

"Naruto's really good to me." She said it as if it was more geared towards her than him.

"Yeah," Sasuke nodded. He gave a curt wave and shortly after, Sakura was gone.

He changed from his regular clothes and crawled into his bed. The day's exhaustion crept all over his body and yet Sasuke found it hard to fall asleep. Every time he closed his eyes, Sakura's face would emerge from the darkness. Her cheeks were wet and her eyes red and puffy as she told him one last time how much she loved him.

It was a frigid morning. The first snowfall from the previous night had left a crunchy layer all along the streets of Konoha. The white scenery only bolded the pink-haired girl standing before him. Her face pleaded with him, haunted him with its sad beauty. As always, her heart was exposed, revealing nothing less than dedication for him. It was undeserving. He did nothing to deserve such overwhelming emotions. She extended it out to him and yet he could not accept. He could not return the deep feelings.

They stood on the field blanketed in snow until the sun began to colour the white canvas a fiery orange. Little words were exchanged, but nothing covered the overwhelming pain engulfing both. Pain for her unrequited love. Pain for his uncomfortable circumstance. How selfish he was and still is.

Before he knew it, a year had passed and Sakura married Naruto. The news came as a shock to him and he never understood his mixed feelings for his two best friends. He was the best man at the ceremony; Naruto wanted it. Sakura seemed pleased with the arrangement, but he wondered how much he still pained her. After their ceremonial kiss, he dropped the subject of him and Sakura from his mind forever.

The sun beat down on his exposed face as the birds' relentless chirping attacked his ears. Morning came as a bitter embrace for Sasuke, the beauty drained through the garishness of the sky, sun, animals- everything.

The clock read 6:30. Sasuke groaned, throwing the covers over his head in defiance. He really needed to buy curtains; or destroy the sun.

By 8 o'clock, he was out the door, heading towards Team 7's usual meeting spot by the park canopy. The three female chunins were already waiting for him when he got there.

"Morning," they said and Sasuke replied with a nod.

"Are there any missions today?" Sachiko asked.

Sasuke shook his head and said, "No. There were some A and B level missions, but I decided to leave that for the genins. We'll train by the waterfall today."

"Sasuke-sensei I saw you at the park yesterday," Kana said as they jogged down the alleyway towards the east gate.

"Oh?" he was far too busy planning out a thorough workout for the girls to take notice of her comment.

"Yeah, I saw you with this lady. You were in one of those swan boats. I didn't think much of it, but then you threw her into the lake and jumped in right after her and I thought that was pretty weird. Is this your idea of a date Sasuke-sensei? I don't think a lot of women would appreciate that."

Sasuke didn't even bother to glance at her and just said, "That's none of your business Kana."

"Does Uchiha-sensei have a girlfriend?" Sachiko chirped, running up beside him.

He did a mental sigh, replying, "No, I don't have time for that. I have my hands full with you three."

"Geez Sasuke-sensei. Aren't you forty and single?"

"Thirty-five Kana. And it's none of your business, but I dare you to address me by my first name again."

"Isn't that lonely?" Sachiko asked.

"I am content with my life. Some people find joy when they are with company while others find joy by themselves. I'm more of the latter and prefer to keep it that way."

"Then who was that lady with you yesterday?" Kana asked.

"An old friend."

"Do you like her?" Sachiko asked

"No."

"Are you going to see her again?" Kana asked.

"None of your business."

"Can we meet her?" Sachiko asked.

"No."

"Why not?" Sachiko asked.

"Because she has nothing to do with you."

"Are you seeing anymore old ladies?" Kana asked. Sasuke didn't like how the word 'old' resonated in his ears.

"None of your business."

"Do you like anyone right now?" Sachiko asked.

"Irrelevant to training."

"Come on Sasuke-sensei, play along-" Kana couldn't finish her sentence because Sasuke hurled a fireball right in her face. She narrowly dodged the hit. The tips of her hair curled and broke off, leaving a pungent burning scent.

"Don't waste my time with useless banter. Now let's get training."

"Yes Sensei…"

-----

"So I hear Hinata's single and ready to mingle," Naruto commented. Most of his concentration was focused on the chess game he was playing with Shikamaru.

"Wow Naruto. He's only gone on two dates with two different women and you already want to send him another one. Check, "Shikamaru swiftly removed the white queen from the board with his black knight.

"There's no harm in trying to deal all your cards at once," Naruto mumbled, biting his lower lip. He was down to one bishop, one knight, four soldiers, and his endangered king,

"Naruto, I'm going to side with Shikamaru. I thought this whole dating game was for me to settle down- not get it on with all the single women in Konoha."

"Yeah, and he hasn't even decided whether or not he likes the women he's dated yet," Shikamaru said.

Naruto moved his king, asking Sasuke, "Well, do you like any of them?"

Sasuke shrugged, crossing his arms.

"Look, I'm just saying if things don't work out between you two, would you be interested in seeing Hinat-"

"No thank you Naruto."

"Why not?" He'd already given up on his chess game and was now focusing his attention towards Sasuke.

"Because it's weird."

"How can you say that? Hinata's a sweet girl!"

"It's weird because she loved you for so long."

"Sasuke, if all men thought like you, there'd be a lot of single people with unrequited love," Shikamaru noted as he flicked Naruto's king off the chessboard with his bishop.

"Just give her a chance, alright? She's super sweet-"

"You already said that."

"Come on Sasuke, what do you have to lose?"

Sasuke pondered that question for a moment, but refrained from answering.

"Hey, I talked to her and she said she's available tonight at, let's say, six?" Naruto flashed Sasuke one of his blue-eyed puppy-dog-look maneuvers. This only made him grimace.

"Fine, just… stop…looking like that. It makes me want to punch you."

Naruto grinned, "Deal."

-----

Sasuke checked his watch for the fifth time, eyeing the entrance to Konoha's Fire Pub as he sat at the bar table. His foot methodically tapped the ground in sharp strikes, each tap getting louder than the next.

The bartender eyed Sasuke, then the entranceway before passing him a drink.

"Stood up?" he asked apologetically, flipping his towel onto his shoulder.

Sasuke sighed, taking the drink as he mumbled, "I hope so."

"Being set up, eh?" the bartender chuckled, "well, I hope she's pretty."

Sasuke downed his drink before responding, "Yeah, well, I hope she doesn't show."

"What time was she supposed to meet you?"

"Six."

The bartender paused a moment, before saying, "Son, you came half an hour ago. It's only been twenty minutes. There's ten more minutes before she shows. Why so impatient?"

"Well, if by six she doesn't show, I'm getting the hell out of here. Buy her a drink on me as a apology."

"Hell, I'd give her a drink on the house if you did such a thing. But I don't think that will be necessary. Is that your lady friend?"

Sasuke turned and saw Hinata standing near the entranceway. She looked around the pub, confused and uncertain. The bartender generously refilled Sasuke's glass and he took a large gulp before motioning for her attention. Hinata stared at Sasuke, looking more confused and uncertain than ever.

She approached him, bowing her head as she said, "Hello Sasuke-kun. Is Naruto-kun here?"

"Hm? No, was he supposed to be?"

"Well, he told me to go to the Fire Pub at six…" her voice trailed off as she looked around the pub once more.

Sasuke made a mental note to strangle Naruto the next time he saw him.

"Hinata, I don't know how to put this, but Naruto asked you to go to the pub to see…me."

"Oh? What is the matter Sasuke-kun? Is this about team assignments?"

"No, it has nothing to do with work."

"Then why did you ask me to come?"

_I didn't,___Sasuke thought bitterly.

"The hokage thought it would be swell if we got to know each other."

"Oh." The heavy weight of disappointment was evident in Hinata's tone of voice.

Sasuke sighed, holding up his glass and asking, "Drink?"

"No thank you. I don't drink."

"Yeah, well, I never drank before either, but you learn to love it either way."

Hinata responded with a confused expression, but Sasuke only shook his head. He motioned for her to take the seat next to him. There a long pause of silence that Sasuke didn't know quite how to end without turning it into awkwardness.

"So…what have you been up to late-"

"Did Naruto set us up on a date?" Hinata interrupted.

"Okay, well, we can talk about that too." Sasuke kept a mental picture of him kicking Naruto continuously in the back of his mind.

"I can't believe he would do this to me," she muttered.

"What's the matter-" Before Sasuke could finish his question, Hinata took his glass and downed the contents with speed faster than his own. Sasuke only stared as she circled the rim of the glass with her finger. Finally, he asked, "Er…drink?"

"No, I don't drink," Hinata insisted, but Sasuke waved for the bartender to refill her glass anyways. Her cheeks were already flushed red.

"I know we don't know each other well Sasuke-kun, so I'm sorry to impose my inner feelings at you so suddenly."

"Don't worry. I'm here to listen to whatever you have to say."

Hinata heaved out a long sigh, her lips pouted like a child's. "He knew I love him…why is he doing this to me?"

"I knew it! That Naruto, I keep telling him-"

"What?"

"Oh, nothing. So what is he doing to you?" The mental picture now switched to him fireballing the helpless Hokage.

"He's forcing me on these dates with strangers all the time- as if I can get over him just like that. It's not that easy Naruto…I keep telling him that, but he won't listen."

"Why did he never return your feelings?"

"He was…we were going to…but then…Sakura came into the picture."

Sasuke felt something sink within him. He knew what was going to come, but he asked anyways. "What do you mean?"

"Well, you know Naruto was always in love with Sakura. Even I knew that, but I couldn't help but try. Then, finally, he responded. He told me he was ready to get over Sakura, but he didn't want to rush anything until he got his own emotions settled. So I waited for him, like I always did. When we were about to…well…suddenly, Sakura came to Naruto and asked him to help her forget you Sasuke. He spent an entire year by her side all the while still being so kind and gentle with me. It was so painful to watch. And when nothing else worked, he asked Sakura to marry him. And…and…she…." Hinata paused to give Sasuke and half-hearted smile, "well, you know what happened afterwards."

Sasuke didn't say anything at first. He rubbed his temples slowly, trying to digest the information he just heard.

"Wow Hinata…I never knew…"

"It's okay. It wasn't your fault."

Sasuke turned to face her. She had a sad beauty that seemed to resonate. "Did he ever…love you back?"

"I think so. I think he was about to, but I guess old feelings are hard to fade away," she said, returning Sasuke's gaze. He watched her examine him with little interest. He felt a sudden pang in his heart. It wasn't chemistry towards Hinata. He felt pity.

"What happens now?" Sasuke finally asked.

Hinata smiled, pushing herself away from the table. She got up and just as he stood to escort her out the door, she turned to him, saying, "Nothing Sasuke. Thank you for the drink."

Sasuke watched as she disappeared into the shadows of the dimly lit street. Something in the back of his mind told him to run; but he didn't know from what. Or who.

-----

_If you want updates on the next chapter, check out my profile. I update it regularly =)_

_Next chapter: TBA (will be up next week! Summer updates will be plenty =) )_


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